Books to Read Before a Challenge, Change, or Crossroads

In 2018, I decided to read 365 books and finished out the year at 390. That’s 128,796 pages, give or take a few. I went through memoirs, Appalachian Trail books, nonfiction discoveries, and more: here are the books that helped me finalize my dream of trying a thru-hike (and here’s the full book list). Whether you want to leave a job to hike, or make another big change, or aren’t sure where to go next, perhaps one of these will jog your mind.

Best weekend reading place in NYC.

Stop Being Scared and Get Out There

Even though I knew someday I’d try the full Appalachian Trail, there were so many little fears or details that would distract me from my goal. (Ticks, no paycheck / job situation on hold, eating gross food, blisters aren’t fun, being cold, etc). These books discuss incredible lives, harrowing journeys, and countless examples of others who have gone through huge changes. My worries definitely fell into perspective when I finished these.

In Extremis: The Life of War Correspondent Marie Colvin, by Lindsey Hilsum

A biography of an amazing female journalist who passed away recently. She didn’t hesitate to run toward the action, even when others would say no. Crazy, messy, brilliant, and I wish I’d met her.

When Breath Becomes Air, by Paul Kalanithi

Whatever you are thinking of doing, it will be easier than writing a memoir while dying from lung cancer. This is short, moving, and emotional, particularly because Paul was a doctor. You’ll remember to be braver and to stop worrying about little things.

Exit West, by Mohsin Hamid

A fiction twist about refugees fleeing problems at home, and everything that comes with that change. People leave through magic doors and appear in other places, but I promise that doesn’t seem weird in the story. Again, a good reminder (even if it’s a novel) that in the long run, I needed to stop worrying.

When to Jump, by Mike Lewis

This book collects countless transitions people have made (mostly between different jobs or pursuits). Trust me, after reading this, it seemed quite reasonable for me to go on a thru-hike. Even if you are completely content with your life right now, some of the examples may make you think.

Learn Something and Challenge Your Mind-set

The Art of Learning: A Journey in the Pursuit of Optimal Performance, by Josh Waitzkin

All about learning (from a chess player) and keeping intellectual pursuits alive in life. If you like to think about thinking, this one is excellent.

The Hour Between Dog and Wolf,  by Laure-Anne Bosselaar

Risk-taking and risk assessment is embedded in us, and while this focuses often on trading jobs, the underlying physiology and psychology was fascinating. I hope I can remember some of the findings if I come to extreme situations on my hike.

Born to Run, by Christopher McDougall

Yes, everything you know is wrong, at least about running. There is some overlap with the hiking crew in this book, but it primarily focuses on trails and ultra-long-distance running. As a hiker, I did come across quite a few tips for endurance-style physical activity, and the story is incredible.

The Happiness of Pursuit, by Chris Guillebeau

I have mentioned this before and I will keep it up. Kind of like the hobby or life path version of When to Jump, this focuses on people taking amazing challenges or interesting life changes. Again, be careful reading if you are content because this may inspire you to make a change.

The Book of  Strange New Things, by Michel Faber

A missionary who goes to another planet to teach the aliens? That is probably the extreme limit of outside one’s comfort zone. This novel was intriguing and different from what I expected, and the characters are so well done. Makes walking for a few months seem like a breeze.

An ideal morning ahead of me

Think Differently about Work, Life, and/or Travel

Walk Through Walls: A Memoir, by Marina Abramović

I’ve read this three times so far and plan to each year. You may have heard of Marina given her performance art, but this digs down so much deeper into her life, relationships, and where her art comes from. (She was ahead of the #vanlife movement too, of course).

Bull*** Jobs: A Theory, by David Graeber

One of my nonfiction favorites of 2018. David dives into what makes people unhappy in jobs, why that’s bad for us, and how this can be improved. Or should everyone quit and be long-term traveling philosopher kings?

Happiness is a Choice You Makeby John Leland

Collected lessons from the longest-lived segments of the world. Their advice and John’s discoveries may make you consider family and relationships a bit differently. I have long thought happiness was a choice and an active daily struggle, at least for me, and it’s been a topic of discussion with friends.

Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel, by Rolf Potts

Exactly what it sounds like. This is a far more intellectual and substantive guide focused on the idea of continual travel. Not just the top packing lists for each climate. Since six months on the AT will be my longest continuous trip, I found this useful in terms of thinking through why I want to keep going.

I won’t have as much time or mental energy for reading on my hike, but I hope to get a few minutes in the evenings. Books are heavy. I’m bringing my Kindle (the Nook was better before it got discontinued). I plan to stash some audiobooks as well for the rainy days when I would rather do nothing and need some motivation.

I am always looking for new recommendations, particularly on the outdoors / adventure front, so send them along if you have any.

Affiliate Disclosure

This website contains affiliate links, which means The Trek may receive a percentage of any product or service you purchase using the links in the articles or advertisements. The buyer pays the same price as they would otherwise, and your purchase helps to support The Trek's ongoing goal to serve you quality backpacking advice and information. Thanks for your support!

To learn more, please visit the About This Site page.

What Do You Think?